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Atlas / Drug / Diethylstilbestrol

Diethylstilbestrol

drug
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Also known as ApstilDietilestilbestrolDistilbeneNSC-3070StilbestroStilbestrolStilbetinStilboesterolTampovaganDiethylstilbesterol (DES)DESDiethyllstilbestroldiethylstilbesterolTrans-diethylstillbestrolSID11112132SID11532921SID17389919SID26747240SID26752777

Summary

Diethylstilbestrol (CHEMBL411) is an approved small-molecule antineoplastic agent (ATC G03CB02) targeting ESR1, ESR2, and ESRRA; indicated across 2 conditions including neoplasm.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: G03CB02 (+2 more)
  • Targets: 5 (ESR1, ESR2, ESRRA…)
  • Indications: 2 conditions
  • Clinical trials: 12
  • Chemistry: 268.3 Da · C18H20O2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL411
NameDiethylstilbestrol
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID448537
ChEBICHEBI:41922
ATCG03CB02, G03CC05, L02AA01
Molecular formulaC18H20O2
Molecular weight268.3
InChIKeyRGLYKWWBQGJZGM-ISLYRVAYSA-N

SMILES: CC/C(=C(/CC)\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)O

IUPAC name: 4-[(E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

ChEBI definition: An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.

Pharmacological roles (ChEBI): antineoplastic agent, carcinogenic agent, xenoestrogen, EC 3.6.3.10 (H+/K+-exchanging ATPase) inhibitor, antifungal agent, endocrine disruptor, EC 1.1.1.146 (11β-hydroxysteroid dehydrogenase) inhibitor, autophagy inducer, calcium channel blocker.

Also known as: Apstil, Diethylstilbestrol, Dietilestilbestrol, Distilbene, NSC-3070, Stilbestro, Stilbestrol, Stilbetin, Stilboesterol, Tampovagan, Diethylstilbesterol (DES), DES

Patent coverage: 206,791 distinct patent families (353,912 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
ESR1Estrogen receptor-αAgonist10.41.7%P03372
ESR2Estrogen receptor-βAgonist9.80.2%Q92731
ESRRAEstrogen-related receptor-αAntagonist5.313.8%P11474
ESRRBEstrogen-related receptor-βAntagonist5.30.2%O95718
ESRRGEstrogen-related receptor-γAntagonist5.30.4%P62508

Broader ChEMBL bioactivity targets: 77 (assay-derived). Sample: Microtubule-associated protein tau, Ubiquitin carboxyl-terminal hydrolase 2, Nuclear receptor ROR-gamma, Survival motor neuron protein, Prelamin-A/C, Inositol monophosphatase 1, Ferritin light chain, Histone-lysine N-methyltransferase 2A, Cysteinyl leukotriene receptor 1, 5-hydroxytryptamine receptor 2B.

Bioactivity

ChEMBL activities: 96 potent at pChembl ≥ 5 of 161 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
ESR210.7EC500.02nMCHEMBL_ACT_206515
ESR110.22EC500.06nMCHEMBL_ACT_206516
ESR110AC500.1nMCHEMBL_ACT_25167224
ESR19.96EC500.11nMCHEMBL_ACT_19211887
ESR19.9Ki0.13nMCHEMBL_ACT_1281824
ESR19.89Ki0.13nMCHEMBL_ACT_1281826
ESR19.7EC500.2nMCHEMBL_ACT_19211878
ESR19.7Ki0.2nMCHEMBL_ACT_25522251
ESR19.66Ki0.22nMCHEMBL_ACT_13340320
ESR19.58Ki0.26nMCHEMBL_ACT_7702721
ESR19.48IC500.33nMCHEMBL_ACT_820735
ESR19.31Ki0.49nMCHEMBL_ACT_1176579
ESR29.2Ki0.63nMCHEMBL_ACT_1176580
ESR19.15IC500.7nMCHEMBL_ACT_25522255
ESR19.04IC500.92nMCHEMBL_ACT_7702720
ESR18.6EC502.5nMCHEMBL_ACT_25522267
ESR18.52IC503nMCHEMBL_ACT_1001016
ESR18.52AC503nMCHEMBL_ACT_25138912
ESR28.4IC504nMCHEMBL_ACT_1001017
ESR28.05EC509nMCHEMBL_ACT_206513
ESR27.99AC5010.2nMCHEMBL_ACT_25175189
ESR17.92EC5012nMCHEMBL_ACT_206514
MAPK16.5Potency316.2nMCHEMBL_ACT_4546067
AOX16.34IC50460nMCHEMBL_ACT_5102802
ABCG26.3IC50500nMCHEMBL_ACT_11000877
ESR26.21IC50610nMCHEMBL_ACT_12102860
ESRRG6.2EC50630nMCHEMBL_ACT_1507451
PGR6.18AC50659.1nMCHEMBL_ACT_25204345
ESR16.11IC50770nMCHEMBL_ACT_12102861
SLC6A36.07Ki851nMCHEMBL_ACT_7702717

Target pathways

Aggregated over 5 target gene(s): ESR1, ESR2, ESRRA, ESRRB, ESRRG.

Top Reactome pathways

19 total, by targets touching each:

PathwayTargetsGenes
Nuclear Receptor transcription pathway5ESR1, ESR2, ESRRA, ESRRB, ESRRG
PIP3 activates AKT signaling2ESR1, ESR2
Constitutive Signaling by Aberrant PI3K in Cancer2ESR1, ESR2
PI5P, PP2A and IER3 Regulate PI3K/AKT Signaling2ESR1, ESR2
ESR-mediated signaling2ESR1, ESR2
Regulation of RUNX2 expression and activity2ESR1, ESRRA
Extra-nuclear estrogen signaling2ESR1, ESR2
Nuclear signaling by ERBB41ESR1
PPARA activates gene expression1ESRRA
Transcriptional activation of mitochondrial biogenesis1ESRRA
SUMOylation of intracellular receptors1ESR1
Ovarian tumor domain proteases1ESR1
TFAP2 (AP-2) family regulates transcription of growth factors and their receptors1ESR1
RUNX1 regulates estrogen receptor mediated transcription1ESR1
RUNX1 regulates transcription of genes involved in WNT signaling1ESR1
Estrogen-dependent gene expression1ESR1
Mitochondrial unfolded protein response (UPRmt)1ESR1
Developmental Lineage of Mammary Gland Luminal Epithelial Cells1ESR1
Developmental Lineage of Mammary Gland Alveolar Cells1ESR1

Dominant GO biological processes

GO termTargets
regulation of DNA-templated transcription5
regulation of transcription by RNA polymerase II5
positive regulation of transcription by RNA polymerase II5
nuclear receptor-mediated steroid hormone signaling pathway4
positive regulation of DNA-templated transcription4
negative regulation of transcription by RNA polymerase II3
signal transduction2
estrogen receptor signaling pathway2
obsolete positive regulation of DNA-binding transcription factor activity2
cellular response to estradiol stimulus2
regulation of gene expression2
cellular response to oxygen-containing compound2
intracellular receptor signaling pathway2
antral ovarian follicle growth1
epithelial cell development1

Indications & clinical

Indications

2 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
neoplasm4MONDO:0005070EFO:0000616

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 12.

Phase distribution

PhaseTrials
Not specified9
PHASE42
PHASE31

Top trials by phase / activity

NCTPhaseStatusTitle
NCT01637896PHASE4TERMINATEDA Comparison Between Paclitaxel-eluting Balloon in Combination With BMS Implantation vs Conventional Balloon and DES Implantation
NCT01925027PHASE4UNKNOWNEfficacy and Safety of Nano+ Polymer-free Sirolimus-Eluting Stent: A Optical Coherent Tomography Study
NCT00316927PHASE3COMPLETEDDexamethasone, Aspirin, and Diethylstilbestrol in Treating Patients With Locally Advanced or Metastatic Prostate Cancer
NCT04859985Not specifiedACTIVE_NOT_RECRUITINGThe SELUTION DeNovo Study
NCT06168422Not specifiedRECRUITINGA Cohort Study of PCI Strategies for Severely Calcified Lesions of Complex Coronary Arteries in the Elderly
NCT03190473Not specifiedTERMINATEDOPTIMIZE IDE for the Treatment of ACS
NCT03223974Not specifiedCOMPLETEDClinical Trial on Safety and Efficacy of Drug-coated Balloon in Treatment of Coronary Bifurcation Lesions
NCT03939468Not specifiedUNKNOWNDrug-Coated Balloon in Combination With New Generation Drug-Eluting Stent for de Novo Diffuse Disease Treatment
NCT04265989Not specifiedUNKNOWNA New Classification and Interventional Therapy for Coronary Artery Ectasia
NCT04842838Not specifiedUNKNOWNComparative Clinical Study of Drug-coating Balloon Strategy and Drug-eluting Stent Strategy
NCT05650450Not specifiedUNKNOWNDrug-Coated Balloon in Combination With New Generation Drug-Eluting Stent in the Treatment of Long Diffuse Coronary Artery Disease
NCT05750771Not specifiedCOMPLETEDComparison of DCB and DES for Severe Calcification of de Novo Lesion in Elderly CHD

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

178 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
ESTRADIOLChEMBL + PubChemPhase 4 (approved)ESR1, ESR2, ESRRA, ESRRB, ESRRG
GENISTEINChEMBL + PubChemPhase 2 (approved)ESR1, ESR2, ESRRA, ESRRB, ESRRG
TAMOXIFENChEMBL + PubChemPhase 4 (approved)ESR1, ESR2, ESRRA, ESRRG
FULVESTRANTChEMBL + PubChemPhase 4 (approved)ESR1, ESR2, ESRRA
MIFEPRISTONEChEMBL + PubChemPhase 4 (approved)ESR1, ESR2, ESRRA
BAZEDOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
BITHIONOLChEMBLPhase 4 (approved)ESR1, ESR2
CISPLATINChEMBLPhase 4 (approved)ESR1, ESR2
ELACESTRANTChEMBLPhase 4 (approved)ESR1, ESR2
ESTETROLChEMBLPhase 4 (approved)ESR1, ESR2
ESTRIOLChEMBLPhase 4 (approved)ESR1, ESR2
ESTRONEChEMBLPhase 4 (approved)ESR1, ESR2
ETHINYL ESTRADIOLChEMBLPhase 4 (approved)ESR1, ESR2
HEXACHLOROPHENEChEMBLPhase 4 (approved)ESR1, ESR2
LASOFOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
MEDROXYPROGESTERONEChEMBLPhase 4 (approved)ESR1, ESR2
PHENOLPHTHALEINChEMBLPhase 4 (approved)ESR1, ESR2
RALOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
SPIRONOLACTONEChEMBLPhase 4 (approved)ESR1, ESR2
ACOLBIFENEChEMBLPhase 3ESR1, ESR2
AFIMOXIFENEChEMBLPhase 3ESR1, ESR2
AMCENESTRANTChEMBLPhase 3ESR1, ESR2
ARZOXIFENEChEMBLPhase 3ESR1, ESR2
BENSERAZIDEChEMBLPhase 3ESR1, ESR2
ALFATRADIOLChEMBLPhase 2ESR1, ESR2
AUS-131ChEMBLPhase 2ESR1, ESR2
BRILANESTRANTChEMBLPhase 2ESR1, ESR2
DAIDZEINChEMBLPhase 2ESR1, ESR2
ERTEBERELChEMBLPhase 2ESR1, ESR2
GTX-758ChEMBLPhase 2ESR1, ESR2
IDOXIFENEChEMBLPhase 2ESR1, ESR2
LEVORMELOXIFENEChEMBLPhase 2ESR1, ESR2
MOXESTROLChEMBLPhase 2ESR1, ESR2
PIPENDOXIFENEChEMBLPhase 2ESR1, ESR2
PRINABERELChEMBLPhase 2ESR1, ESR2
STALLIMYCINChEMBLPhase 2ESR1, ESR2
BosentanPubChemApprovedESR1, ESR2
DihydroergotaminePubChemApprovedESR1, ESR2
FidaxomicinPubChemApprovedESR1, ESR2
PropoxyphenePubChemApprovedESR1, ESR2
PyrazinamidePubChemApprovedESR1, ESR2
ACETOPHENAZINEChEMBLPhase 4 (approved)ESR1
ALECTINIBChEMBLPhase 4 (approved)ESR1
APOMORPHINEChEMBLPhase 4 (approved)ESR1
ARIPIPRAZOLEChEMBLPhase 4 (approved)ESR1
ASPIRINChEMBLPhase 4 (approved)ESR1
AZTREONAMChEMBLPhase 4 (approved)ESR1
BELINOSTATChEMBLPhase 4 (approved)ESR1
BENZBROMARONEChEMBLPhase 4 (approved)ESR1
BEXAROTENEChEMBLPhase 4 (approved)ESR1
BISACODYLChEMBLPhase 4 (approved)ESR1
BROMOCRIPTINEChEMBLPhase 4 (approved)ESR1
BUTOCONAZOLEChEMBLPhase 4 (approved)ESR1
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)ESR1
CASPOFUNGINChEMBLPhase 4 (approved)ESR1
CEFADROXILChEMBLPhase 4 (approved)ESR1
CEFEPIMEChEMBLPhase 4 (approved)ESR1
CEFTAZIDIMEChEMBLPhase 4 (approved)ESR1
CERIVASTATINChEMBLPhase 4 (approved)ESR1
CHLOROTRIANISENEChEMBLPhase 4 (approved)ESR1

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot